Cavomycins A–C, Linear Oligomer Depsipeptides from an Annelid-Associated Streptomyces cavourensis

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-03-04 DOI:10.1021/acs.jnatprod.3c01275

Weihong Wang, JunI Lee, Eun Roh, Gauri Shetye, Jin Cao, James McAlpine, Guido Pauli, Scott Franzblau, Thi Hanh Nguyen Vu, Ngoc Tung Quach, Eunseok Oh, Kyu-Hyung Park, Chanyoon Park, Youbin Cho, Hyeseon Jang, SongJoo Han, Hiyoung Kim, Sanghyun Cho, Quyet-Tien Phi and Heonjoong Kang*,

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Abstract

Three unique linear oligomeric depsipeptides, designated as cavomycins A–C (1–3), were identified from Streptomyces cavourensis, a gut bacterium associated with the annelid Paraleonnates uschakovi. The structures of these depsipeptides were determined through a combination of spectroscopic methods and chemical derivatization techniques, including methanolysis, the modified Mosher’s method, advanced Marfey’s methods, and phenylglycine methyl ester derivatization. The unique dipeptidyl residue arrangements in compounds 1–3 indicate that they are not degradation products of valinomycin. Compound 2 and its methylation derivative 2a exhibited antiproliferative activity against PANC-1 pancreatic cancer cells with IC₅₀ values of 1.2 and 1.7 μM, respectively.

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鱼腥酵母菌 A-C，一种与蛛形纲动物相关的鱼腥酵母菌的线性寡聚体去肽。

从一种与环带藻类 Paraleonnates uschakovi 相关的肠道细菌 Streptomyces cavourensis 中鉴定出了三种独特的线性低聚体去肽类物质，命名为鱼腥酵母菌素 A-C（1-3）。这些去肽类化合物的结构是通过光谱方法和化学衍生技术（包括甲醇分解法、改进的莫舍尔法、先进的马菲法和苯甘氨酸甲酯衍生法）相结合确定的。化合物 1-3 中独特的二肽残基排列表明它们不是缬氨霉素的降解产物。化合物 2 及其甲基化衍生物 2a 对 PANC-1 胰腺癌细胞具有抗增殖活性，IC50 值分别为 1.2 和 1.7 μM。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.